Eastern Shore

Home to legendary seafood, gorgeous beaches, and an endless supply of hidden treasures and surprises, the Eastern Shore offers a world of possibilities.

The beaches, islands and waterways makes for a relaxing yet adventurous vacation. Bird watch, enjoy the horses, explore its idyllic small towns, lose yourself in its nature preserves and marshlands, or just let the time slip away on its sandy beaches.

10 Things to Do on the Eastern Shore

Maryland’s Eastern Shore is home to spectacular sunsets, world-class seafood and produce, nature, history and so much more. Take the trip of a lifetime to Maryland’s Eastern Shore and check these things to do off your list!

1 Watch a rocket launch while camped with wild horses, Assateague Island National Seashore and State Park

Camping at Assateague, home of the famous wild horses, always makes for a memorable vacation, but try visiting when NASA’s nearby Wallops Island flight facility is due to launch. There’s nothing quite like the site of a rocket hurtling towards the heavens to put the exclamation point on an Assateague adventure.

2 Visit Chesapeake City Historic District

Historic Chesapeake City is on the National and Maryland Historic Registries. This beautiful town features lovely restored homes, Inns and B&Bs. You will find great shops, eateries, Canal Museum, bike trail and outdoor summer concerts.

3 Marvel at the untamed Chesapeake at Blackwater National Wildlife Refuge

Stand in awe under a sky dotted with eagles and lose yourself in Blackwater’s primeval forests. Blackwater National Wildlife Refugeis home to three distinct ecosystems and a stunning array of wildlife.

4 Go West, young man, to Frontier Town, Whaleyville

Just a stone’s throw from Assateague and Ocean City is Frontier Town, where the Old West is alive and well. A Maryland institution for more than 50 years, pan for gold, take a ride on a stagecoach, and enjoy the six-iron thrills of Frontier Town’s legendary Old West show.

5 Walk in the footsteps of Harriet Tubman

“The Moses of Her People,” Harriet Tubman escaped from slavery but returned to her Eastern Shore home to lead others to freedom, becoming perhaps the most famous conductor on the Underground Railroad. You can retrace her historic journeys along the Harriet Tubman Underground Railroad Byway and the soon to open Harriet Tubman Underground Railroad State Park.

6 Dine at the Bartlett Pear Inn, Easton

Offering up sumptuous feasts of locally sourced foods and artisanal cocktails that will wow the most discerning pallet, chef Jordan Lloyd’s Bartlett Pear Inn was named one of the 100 Very Best Restaurants by Washingtonian magazine. Consider combining dinner with a stay at adjoining boutique hotels.

7 Play the ponies then hit the slots at Ocean Downs, Berlin

There’s nothing quite like a day at the races, and Ocean Downs’ historic trotters track is a one-of-a-kind raceway. After the races, hit the casino for slots, simulcast horse-racing and great food at Ocean Downs. Then treat yourself to a first-rate steak at Pacers.

8 Paddle the Indian Water Trails on a guided canoe tour of Bending Water Park, Marion Station

Follow a native guide through Bending Water Park while paddling this traditional home of the Accohannock Tribe. Miles of trails skirt pristine wetlands with no manmade structures in site. Dip your paddle and get a taste of unspoiled Maryland wilderness.

9 Charter a boat and head out on the Chesapeake for an angling adventure

Chesapeake Bay rockfish make for some of the best fishing in the world and there’s a flotilla of charters on the Eastern Shore just waiting to take you out for a day on the Bay.

Photo By: Clark Vandergrift

10 Catch the annual National Hard Crab Derby, Crisfield

Crisfield is an amazing destination 365 days a year (and 366 in leap years!), but there’s something about the National Hard Crab Derby that makes for a must-do adventure. In addition to the great crustacean race, the Derby includes parades, a carnival and the Miss Crustacean contest.